Quincy Larson has a pretty reasonable approach to encrypting your data:
And when I use the terms “private” or “secure”, I mean reasonably so. The reality is that — as long as humans are involved — no system will ever be 100% private or 100% secure.
His list is short and pretty unobtrusive. For normal people, it's key to balance the mental cost verses the potential benefit of encrypting everything. A password manager is a no-brainer. Two Factor Authentication is quite a hurdle for many people. Using an encrypted chat service may be a complete deal breaker if they don't have anyone else on the service to chat with.